Triethylamine → 9-Methoxymethyl-9-(dimethylphenylsilyl)oxymethyl-fluorene

HRID 2416163Notes

Reaction equation

HRID 2416163 reaction equation
[CH3:1][O:2][CH2:3][C:4]1([CH2:17][OH:18])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2.C(N(CC)CC)C.[CH3:26][Si:27](Cl)([CH3:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>ClCCl>[CH3:1][O:2][CH2:3][C:4]1([CH2:17][O:18][Si:27]([CH3:34])([CH3:26])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13029ChlorodimethylphenylsilaneHCID 226391039-(Methoxymethyl)-9H-fluorene-9-methanol

Product 1

HCID 693043209-Methoxymethyl-9-(dimethylphenylsilyl)oxymethyl-fluoreneYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 g of 9-methoxymethyl-9-hydroxymethyl-fluorene (4.2 mmol) was dissolved in 20 ml of dichloromethane. The solution was cooled in ice-water bath, and 1 ml of triethyl amine (7 mmol) was added thereto. After stirring for 5 minutes, 1 ml of dimethylphenylsilyl chloride (6.2 mmol) was added drop-wise, and the mixture was stirred for further 2 hours, followed by stirring at room temperature for 1 hour. The reaction mixture was washed with water, and the organic layer separated was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated, and the remainder was purified through column chromatography to give 1.44 g of concentrate (yield 92.4%).

Workup

  1. stirringthe mixture was stirred for further 2 hours
  2. stirringby stirring at room temperature for 1 hour
  3. washThe reaction mixture was washed with water
  4. customthe organic layer separated
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated
  8. customthe remainder was purified through column chromatography
  9. customto give 1.44 g
  10. concentrationof concentrate (yield 92.4%)

Sources & evidence

ORD record
ord-ca46a4fc2b7c47c891f230b0201e6c29
Source dataset
uspto-grants-2004_11
Patent number
US06822109B2

Reaction notes

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